Mechanism of the oxidation of alcohols by oxoammonium cations.

@article{Bailey2007MechanismOT,
  title={Mechanism of the oxidation of alcohols by oxoammonium cations.},
  author={William F Bailey and James M Bobbitt and Kenneth B. Wiberg},
  journal={The Journal of organic chemistry},
  year={2007},
  volume={72 12},
  pages={4504-9}
}
The mechanism of the oxidation of primary and secondary alcohols by the oxoammonium cation derived from 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) has been investigated computationally at the B3LYP/6-31+G* level, along with free energies of solvation, using a reaction field model. In basic solution, the reaction involves formation of a complex between the alkoxide anion and the oxoammonium cation in a pre-oxidation equilibrium wherein methoxide leads to a much larger formation constant than… CONTINUE READING